ASYMMETRIC DIELS-ALDER REACTION OF CYCLOPENTADIENE AND METHYL ACRYLATE CATALYZED BY CHIRAL ORGANOALUMINUM REAGENTS

被引:55
作者
MARUOKA, K [1 ]
CONCEPCION, AB [1 ]
YAMAMOTO, H [1 ]
机构
[1] NAGOYA UNIV, FAC ENGN, DEPT APPL CHEM, NAGOYA 46401, JAPAN
关键词
D O I
10.1246/bcsj.65.3501
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric Diels Alder reaction of cyclopentadiene and methyl acrylate has been effected with high enantioselectivity under the influence of catalytic amounts of chiral organoaluminum reagents.
引用
收藏
页码:3501 / 3503
页数:3
相关论文
共 35 条
[1]   SYNTHESIS OF ISOPINOCAMPHEYLHALOGEN BORANES AND THEIR USE AS CHIRAL CATALYSTS FOR ASYMMETRICAL DIELS-ALDER REACTIONS [J].
BIR, G ;
KAUFMANN, D .
TETRAHEDRON LETTERS, 1987, 28 (07) :777-780
[2]   ASYMMETRIC DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH N-CROTONOYL AND N-ACRYLOYL-4,4-DIMETHYL-1,3-OXAZOLIDIN-2-ONE, MEDIATED BY CHIRAL LEWIS-ACIDS [J].
CHAPUIS, C ;
JURCZAK, J .
HELVETICA CHIMICA ACTA, 1987, 70 (02) :436-440
[3]   1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].
COREY, EJ ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967
[4]   PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].
COREY, EJ ;
IMWINKELRIED, R ;
PIKUL, S ;
XIANG, YB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495
[5]   SELF-INDUCED DIASTEREOSELECTIVE OXIDATION OF VINYL SULFIDES BEARING A CHIRAL HYDROXY GROUP AS A WAY OF PREPARATION OF OPTICALLY-ACTIVE SULFINYL DIENOPHILES AND THEIR USE IN THE ASYMMETRIC DIELS-ALDER REACTION TO CYCLOPENTADIENE [J].
DELUCCHI, O ;
LUCCHINI, V ;
MARCHIORO, C ;
VALLE, G ;
MODENA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1457-1466
[6]   CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS [J].
FURUTA, K ;
SHIMIZU, S ;
MIWA, Y ;
YAMAMOTO, H .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1481-1483
[7]   ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION CATALYZED BY CHIRAL ACYLOXYBORANE COMPLEX [J].
FURUTA, K ;
KANEMATSU, A ;
YAMAMOTO, H ;
TAKAOKA, S .
TETRAHEDRON LETTERS, 1989, 30 (51) :7231-7232
[8]   ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY CHIRAL ALKOXYALUMINIUM DICHLORIDE [J].
HASHIMOTO, S ;
KOMESHIMA, N ;
KOGA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (10) :437-438
[9]   2-POINT-BINDING ASYMMETRIC DIELS-ALDER CATALYSTS - AROMATIC ALKYLDICHLOROBORANES [J].
HAWKINS, JM ;
LOREN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7794-7795
[10]   CHARACTERIZATION OF THE CHIRAL TITANIUM REAGENT PREPARED FROM THE TARTRATE-DERIVED CHIRAL DIOL AND TITANIUM DICHLORIDE DIISOPROPOXIDE [J].
IWASAWA, N ;
HAYASHI, Y ;
SAKURAI, H ;
NARASAKA, K .
CHEMISTRY LETTERS, 1989, (09) :1581-1584